2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Chemical Properties

Melting point:

208.0 to 212.0 °C

Boiling point:

362.0±37.0 °C(Predicted)

Density 

1.474±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Sparingly)

form 

powder to crystal

pka

11.09±0.70(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C11H10ClN3OS/c1-6-3-2-4-7(12)9(6)15-10(16)8-5-14-11(13)17-8/h2-5H,1H3,(H2,13,14)(H,15,16)

InChIKey

VVOXTERFTAJMAA-UHFFFAOYSA-N

SMILES

S1C(C(NC2=C(C)C=CC=C2Cl)=O)=CN=C1N

CAS DataBase Reference

302964-24-5(CAS DataBase Reference)

Safety Information

HS Code 

29333990

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Usage And Synthesis

Uses

2-Amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide, is a precursor in the synthesis of Dasatinib (D193600), a protein tyrosine kinase inhibitor, and also for 2-Amino-thiazole-5-carboxylic Acid Phenylamide Derivatives, used as potent and selective anti-tumor drugs.

Synthesis

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is synthesised using Tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-YL)carbamate as a raw material by chemical reaction. The specific synthesis steps are as follows:
To the stirred solution of trifluoroacetic acid (TFA) (250.0 mL) added tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)carbamate 23 (25.0 g, 0.07 mol) and stirred for 2h at 25-30°C. Reaction completion was confirmed by TLC, distilled the TFA and the residue was diluted with ethyl acetate (EtOAc),(250.0 mL). Ethyl acetate layer was washed with saturated NaHCO3 solution (2 X 25.0 mL), water, followed bysaturated NaCl solution (125.0 mL). Ethyl acetate layer was dried over Na2SO4 and concentrated. The residual mass on treatment with methyl tert-butyl ether (250.0) gave 9 (16.2 g, 89percent) [11].IR (KBr, cm-1): 3382.4, 3284.85 (N-H), 1627.02 (C=O), 1644; 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm(J, Hz): 9.63 (s, 1H, thiazole-H), 7.86 (s, 1H), 7.60 (s, 2H, -NH2), 7.38 (dd, 1H, J =7.5, 4.02, Ar-H), 7.20-7.22 (m,2H, J =7.5, Ar-H), 2.20 (s, 3H, Ar-CH3); 13C NMR spectrum (100 MHz, DMSO-d6), δ, ppm: 172.2, 159.6, 143.2,138.9, 133.7, 132.5, 129.0, 128.0, 127.0, 120.7 and 18.3; MS (ESI) m/z 268.0 [M + H] + [11].

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide(302964-24-5)Related Product Information

• Dacomitinib (PF299804)
• Methyl 2-aminothiazole-5-carboxylate
• ETHYL 2-(TERT-BUTOXYCARBONYLAMINO)THIAZOLE-5-CARBOXYLATE
• 2-N-BOC-AMINO-THIAZOLE-5-CARBOXYLIC ACID
• 2-Chloro-6-methylaniline
• (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide
• Dasatinib monohydrate
• (E)-3-Ethoxyacryloyl chloride
• N,N-Dimethylformamide
• N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide
• Dasatinib
• ALTRENOGEST
• Epichlorohydrin
• N-Methylformamide
• Glycine
• N-Deshydroxyethyl Dasatinib
• Dasatinib Impurity 33
• 2-[[6-[4-(2-Hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxylic acid